Cudraxanthone D - ≥98% , CAS No.96552-41-9

CAS: 96552-41-9 Cat. No.: C1014367 PubChem CID: 11611248

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Especificações e pureza

≥98%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥98%

Nomes e identificadores

• Sorrisos canónicos: CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(O2)C(=C(C=C3O)OC)C(C)(C)C=C)O)O)C
• IUPAC Name: 2,3,8-trihydroxy-6-methoxy-5-(2-methylbut-3-en-2-yl)-1-(3-methylbut-2-enyl)xanthen-9-one
• InChIKey: UIIGEZZURHDEDK-UHFFFAOYSA-N
• INCHI: 1S/C24H26O6/c1-7-24(4,5)20-17(29-6)10-14(25)19-22(28)18-13(9-8-12(2)3)21(27)15(26)11-16(18)30-23(19)20/h7-8,10-11,25-27H,1,9H2,2-6H3
• SMILES isoméricas: CC(=CCC1=C(C(=CC2=C1C(=O)C3=C(O2)C(=C(C=C3O)OC)C(C)(C)C=C)O)O)C
• PubChem CID: 11611248

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Benzopyrans
      • Subclass 1-benzopyrans
        • Level5 Dibenzopyrans
          • Level6 Xanthenes
            • Level7 Xanthones
              • Level8 8-prenylated xanthones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Dibenzopyrans - Xanthenes - Xanthones
• Direct Parent: 8-prenylated xanthones
• Alternative Parents: Chromones Anisoles Pyranones and derivatives Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Heteroaromatic compounds Polyols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 8-prenylated xanthone - Chromone - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Vinylogous acid - Polyol - Ether - Oxacycle - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 410.500 g/mol
• XLogP3: 6.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 410.173 Da
• Monoisotopic Mass: 410.173 Da
• Topological Polar Surface Area: 96.200 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 681.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated immunoassay or bioassay protocols are provided in the Product Data for this item.

General laboratory workflows (informational):

• Analytical stock preparation:
  • Weigh in low-light conditions; dissolve at 10–50 mM in anhydrous DMSO; vortex and sonicate briefly if needed.
  • Filter through 0.22 μm PTFE for LC applications.
• LC–MS method development:
  • Column: C18, 2.1 × 100 mm, 1.7–3 μm.
  • Mobile phases: A = water + 0.1% formic acid; B = acetonitrile (or methanol).
  • Gradient: 10% B to 95% B over 10–15 min; detect 254–360 nm and full-scan MS.
• Solid-phase purification:
  • Use silica or reversed-phase cartridges; elute with hexane/EtOAc or water/ACN systems.

These are generalized suggestions for xanthone-type analytes. Adapt conditions to your instrumentation and regulatory environment. For any specific, validated protocol, refer to your lab’s SOPs or request application support.

Biological Roles

No medical or clinical claims are made. The following describes general, literature-level context for the chemical class.

General background (literature):

• Natural occurrence: Cudraxanthone-type metabolites are reported from plants in the Moraceae family. They belong to the xanthone polyketide lineage.
• Chemical ecology: Prenylation increases lipophilicity and membrane affinity, features often associated with plant secondary metabolites that interact with microbial or herbivore systems.
• Biochemical features:
  • Phenolic groups can undergo redox cycling and radical scavenging in vitro, a behavior common to polyphenolic scaffolds.
  • Conjugated xanthone chromophore supports UV absorption/photophysical interactions, which may be relevant in plant photoprotection.
• Research uses: Employed as standards in phytochemical profiling, aiding identification and quantification of xanthone constituents in botanical extracts via LC–MS/MS libraries.

Note: Any references to bioactivity in the literature should be interpreted strictly as in vitro or preclinical observations. This product is provided strictly for research use in laboratory settings.

Buffer Applications

Not typically applicable. Cudraxanthone D is a hydrophobic, non-buffering small molecule and does not serve as a pH buffer component.

Practical notes (general):

• If incorporation into aqueous systems is required (e.g., in vitro assays), dissolve first in DMSO or EtOH to prepare a concentrated stock, then dilute into the buffered medium while maintaining a low final co-solvent percentage (commonly ≤1–2%).
• Buffer choice (PBS, HEPES, phosphate, acetate) should be dictated by the biological/analytical assay; the compound itself does not define buffering capacity.

Green Alternatives

Although Cudraxanthone D itself is not a solvent or bulk reagent, greener choices can be made for its handling, purification, and analysis.

Greener solvent choices for dissolution and chromatography (general guidance):

• Replace DMF with DMSO or propylene carbonate when feasible (lower toxicity concerns than DMF; note higher viscosity for propylene carbonate).
• Use ethanol or isopropanol in place of methanol for routine work when UV sensitivity allows.
• Favor ethyl acetate or methyl tert-butyl ether (MTBE) over dichloromethane for extractions, considering volatility and safety tradeoffs.
• For reversed-phase LC, prefer water/ethanol gradients where detection and backpressure permit; otherwise, acetonitrile often offers a good balance of performance and environmental impact compared to halogenated solvents.

Comparison snapshot (general; not item-specific):

• Ethyl acetate vs DCM: Similar elution strength in normal phase; EtOAc is biodegradable and less hazardous but has higher boiling point.
• Ethanol vs Methanol: Slightly less toxic; compatible with many detectors; higher viscosity may limit UHPLC flow rates.
• MTBE vs DCM: Lower density and lower halogen content; flammable and peroxidizable—store with inhibitors and check before concentration.

Operational tips:

• Concentrate solutions under reduced pressure at moderate temperatures to limit energy use and oxidative degradation.
• Reuse silica cartridges and adopt prep-RP recycling where possible to reduce solid waste.

Pharmaceutical Uses

No therapeutic or clinical use is claimed. The material is provided for research use only.

Relevant non-clinical, laboratory contexts:

• Analytical reference standard: Can be used to qualify or validate chromatographic methods for botanical raw materials containing xanthones (system suitability standards, calibration curves).
• Formulation research (in vitro): Solubility enhancement studies (e.g., with cyclodextrins, micelles, or co-solvents) to understand how prenylated polyphenols behave in delivery matrices. These are research exercises, not for human or veterinary use.
• Impurity profiling/marker compound: Potential role as a marker analyte in QC of research-grade plant extracts.

Regulatory note: No pharmacopeial monograph is indicated for this specific compound in the provided data. For any GMP or clinical pathway requirements, a separate qualification and sourcing process would be necessary.

Physical Properties

Item-specific properties (from Product Data):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for prenylated xanthones (informational, not item specifications):

• Physical state: Typically a yellow to orange crystalline solid or amorphous powder due to extended conjugation of the xanthone core.
• Melting point: Often observed in the ~180–250 °C range for polyhydroxy xanthones; exact value depends on substitution pattern.
• Solubility profile:
  • Water: Poorly soluble owing to the hydrophobic prenyl group(s) and polyaromatic core.
  • Organic solvents: Soluble in DMSO, DMF, hot methanol/ethanol, acetone, and acetonitrile; limited solubility in nonpolar hydrocarbons unless derivatized.
• Acid–base behavior: Phenolic OH groups exhibit weak acidity (pKa typically ~8–10 across phenolic xanthones; literature values vary with substitution).
• UV–Vis: Strong absorption in the near-UV/visible due to the xanthone chromophore; multiple maxima are common around 240–420 nm depending on substituents (literature trend; not a specification).
• Stability: Generally stable as a solid at ambient conditions; phenolic/prenylated systems can be sensitive to strong base, prolonged light, or oxidants.

Note: For exact, item-specific values (mp, solubility limit, UV cutoff, elemental analysis), consult the item’s CoA/Spec Sheet.

Quality and Grades

Item-specific details (from Product Data):

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Context and what to expect for this class of product (informational):

• Natural product reference standard: For small molecules like Cudraxanthone D, suppliers often provide an HPLC purity percentage and supporting spectra (1H/13C NMR, HRMS, and chromatograms). When available, these confirm identity and purity suitable for discovery, metabolomics, or analytical calibration.
• HPLC/UPLC suitability: High-purity material minimizes baseline drift and co-eluting impurities in quantitative analysis. If your application is quantitative, request the most recent CoA with HPLC trace and method.
• Stability and assay: Phenolic prenylated xanthones may slowly oxidize in solution; if purity is high on receipt, maintain aliquots under inert atmosphere or reduced light for analytical reproducibility.
• Identity confirmation: Match CAS (96552-41-9) and PubChem CID (11611248) with your internal LIMS. If the product lists an InChIKey on the CoA, prefer the 27-character hashed key for unambiguous digital identity.

What the grade implies (general):

• Research-grade materials are intended for laboratory R&D only (not GMP). If you require GMP, pharmacopeial conformity, or impurity profiling, contact us for feasibility or custom synthesis options.

Reaction and Applications

This compound is primarily a research analyte and natural product standard rather than a general-purpose reagent. Nevertheless, the xanthone core and phenolic/prenyl functionality enable useful derivatizations and analytical applications.

Applications (research/laboratory):

• Analytical reference standard: Use for method development and calibration in LC–UV/LC–MS metabolomics or phytochemical profiling of Moraceae extracts.
• Structure–property studies: Probe effects of prenylation and phenolic substitution on photophysics (UV–Vis), redox behavior (cyclic voltammetry), and chromatographic retention.
• Derivatization chemistry:
  • Phenolic protection/alkylation: Acetylation, methylation (e.g., MeI/Ag2O; Me2SO4/K2CO3) to tune solubility and stability.
  • O-glycosylation (literature): Activation of glycosyl donors under Lewis-acid or phase-transfer conditions to access glyco-derivatives for SAR.
  • Prenyl transformations: Epoxidation or hydroboration–oxidation on the prenyl double bond to map reactivity or generate more polar analogs.
• Photophysical assays: The extended conjugation of the xanthone chromophore makes it suitable for fluorescence/UV quenching studies and binding interactions with biomimetic hosts (e.g., cyclodextrins) in vitro.

Practical tips:

• Minimize exposure of solutions to light and air; use amber vials and inert gas where practical.
• For clean alkylation, pre-form phenolates with mild base (K2CO3/Cs2CO3) in polar aprotic solvents; avoid over-alkylation by controlling equivalents and time.
• For LC–MS methods, small amounts of acid (0.05–0.1% formic acid) can sharpen peaks and improve ionization in positive or negative modes depending on the derivative.

Reaction Conditions

General laboratory conditions for transformations on phenolic, prenylated xanthones (literature-level guidance; not item-specific specifications):

• O-Methylation/O-Benzylation:

  • Base: K2CO3 or Cs2CO3 (1.5–3.0 eq)
  • Electrophile: MeI, Me2SO4, or BnBr (1.2–2.0 eq)
  • Solvent: Acetone, acetonitrile, or DMF
  • Temperature/Time: 20–60 °C, 2–16 h
  • Notes: Exclude moisture to enhance selectivity; monitor by TLC/HPLC.

• Acetylation (protection):

  • Reagents: Ac2O (3–5 eq), catalytic DMAP, pyridine or Et3N
  • Solvent: DCM or EtOAc
  • Temperature: 0 °C to rt, 1–4 h
  • Notes: Quench with aqueous NaHCO3; avoid over-acylation of adventitious alcohols.

• Epoxidation of prenyl alkene:

  • Reagent: mCPBA (1.1–1.5 eq)
  • Solvent: DCM or toluene
  • Temperature: 0–25 °C, 1–3 h
  • Notes: Buffer with NaHCO3 to minimize phenolic oxidation; verify regioselectivity.

• Hydroboration–oxidation:

  • Reagents: 9-BBN or BH3·THF; then H2O2/NaOH
  • Solvent: THF or 2-MeTHF (green alternative)
  • Temperature: 0–25 °C
  • Notes: Protect phenols if competitive reactions occur; yields are substrate-dependent.

• Reversed-phase prep-LC isolation/purification:

  • Mobile phase: Water/ACN (or Water/EtOH) with 0.05–0.1% formic acid or ammonium acetate
  • Detection: UV 254–360 nm (xanthone chromophore)
  • Notes: Use low-light conditions to limit photodegradation.

Expected yields vary widely with substitution; consult primary literature for close structural analogs.

Safety and Handling

Item-specific safety (from Product Data):

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory handling guidance (for small-molecule phenolic xanthones; informational only—defer to SDS):

• PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin and eye contact with powders/solutions.
• Engineering controls: Handle powders in a fume hood to minimize inhalation and dusting. Use closed containers for weighing and transfers.
• Incompatibilities: Avoid strong oxidizing agents (prenyl/phenolic groups are oxidizable), strong bases (may induce rapid phenolate formation and side reactions), and prolonged exposure to light/air if solution is prepared.
• Spill/cleanup: For solids, gently collect using disposable tools, avoiding aerosolization; wipe residues with solvent-dampened absorbent. For solutions, absorb with inert material and dispose per institutional guidelines.
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical assistance.
• Waste: Dispose as organic laboratory waste. Phenolic compounds may require specialized handling per local regulations.

Always consult the product’s SDS for authoritative hazard classification and response measures.

Solvent Selection

Cudraxanthone D is a polyaromatic, phenolic natural product; it behaves as a moderately lipophilic analyte with hydrogen-bond donor capability.

General solvent guidance (literature-based for prenylated xanthones):

• Stock solutions:
  • Prefer DMSO or DMF for concentrated stocks (e.g., 10–50 mM), then dilute into assay medium or mobile phase just before use.
  • For spectroscopic work, MeOH, EtOH, or ACN provide good UV transparency.
• Chromatography:
  • Normal phase (silica): Elute with hexane/EtOAc or toluene/EtOAc mixtures; polar modifiers (MeOH) assist with strongly retained phenolic forms.
  • Reversed phase (C18): Water/ACN or Water/MeOH with 0.1% formic acid or ammonium acetate buffers stabilize peak shape and ionization (for LC–MS).
• Miscibility and polarity: Poorly water-soluble; co-solvent systems are recommended when aqueous media are required. Maintain final DMSO content typically ≤1–2% in bioassays (general lab practice).

Quick comparison (general):

• DMSO: Maximum solubilization; hygroscopic; strong UV cutoff >260 nm.
• ACN: Good solubility, LC–MS friendly, low viscosity.
• MeOH/EtOH: Widely compatible with spectroscopic and prep workflows; potential for hydrogen bonding to phenols affecting retention.

Note: For preparative work, avoid prolonged heating in protic solvents to limit transesterification or oxidative side reactions on the prenyl/phenolic sites.

Storage and Reconstitution

Item-specific (from Product Data):

• Recommended storage: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (informational; complements but does not override Product Data):

• Solid storage: Keep tightly closed in a dry, well-ventilated place. Protect from excessive light. Consider storing in amber glass with desiccant to limit moisture uptake and oxidative changes.
• Solution handling: If solutions are prepared (e.g., in DMSO/MeOH), aliquot into amber vials, purge with inert gas if available, and store cold (e.g., −20 °C) to prolong stability. Avoid repeated freeze–thaw cycles by preparing single-use aliquots.
• Reconstitution:
  • Start with anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM), then dilute into the working solvent or buffer immediately before use.
  • If particulate persists, warm gently (≤40 °C) and sonicate briefly; avoid prolonged heating.

Always refer to the product’s CoA and SDS for definitive handling and stability information. Research use only.

Structure and Identity

Brief overview: Cudraxanthone D is a prenylated xanthone-type natural product commonly reported from Moraceae species (e.g., Cudrania/Cudraflava spp.), used in research as a reference standard and small-molecule probe.

Item-specific (from Product Data):

• Product Name: Cudraxanthone D (SKU: C1014367)
• CAS: 96552-41-9
• PubChem CID: 11611248
• InChIKey: 360647 (as provided; note this is not the typical 27-character hashed string; consult CoA/Spec Sheet for the definitive identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general literature description of the class):

• Core scaffold: Xanthone (dibenzo-γ-pyrone) tricyclic system consisting of two benzene rings fused through a central pyranone.
• Substituents (typical of “cudraxanthones”): One or more prenyl/geranyl chains and multiple phenolic –OH groups positioned on the aromatic rings.
• Functional groups: Conjugated ketone (C=O) within the xanthone core; phenols (acidic), isoprenyl alkenes (electron-rich alkenes that can undergo electrophilic addition/oxidation).
• Stereochemistry: The xanthone core is planar; prenyl side chains may feature E/Z alkene geometry where present but are typically not stereogenic centers unless further functionalized.

2D depiction in words (literature/general): Two substituted phenyl rings flanking a central 1,4-benzopyran-2-one; phenolic OH groups appear ortho/para to the carbonyl across the rings; a prenyl chain is attached to an aromatic carbon (commonly C-2/C-4/C-8 positions in xanthones), extending as an isopentenyl unit.

Synthetic Utility

While not a routine building block, Cudraxanthone D embodies reactive motifs that enable purposeful derivatization and serve as a platform for structure–activity exploration.

Reactive handles and typical transformations (literature/general):

• Phenolic OH groups:
  • Protection as acetates, benzoates, methyl/benzyl ethers for sequential functionalization.
  • O-alkylation/O-acylation under mild base (K2CO3/Cs2CO3) in polar aprotic media.
  • Chelation/activation for C–O cross-coupling (e.g., aryl–O via diaryliodonium salts) after suitable activation.
• Xanthone carbonyl:
  • Participation in nucleophilic additions (less common due to conjugation), or conversion to imines/Schiff bases with appropriate amines after activation.
  • Photochemical engagement due to the conjugated chromophore, enabling excited-state studies.
• Prenyl double bond(s):
  • Electrophilic additions (halogenation, hydrohalogenation), epoxidation, dihydroxylation, or hydroboration–oxidation to generate diversified side chains.

Retrosynthetic value:

• Serves as a benchmark for assembling prenylated xanthones via Friedel–Crafts acylation–cyclization or oxidative coupling routes from polyhydroxybenzenes and C5 isoprenoid units.

Utility in method development:

• A challenging analyte for testing selectivity in phase-transfer catalysis, late-stage O-functionalization, and minimally basic reaction conditions that preserve phenolic integrity.

Target Specificity

Not applicable. This product is a small-molecule natural product standard, not an antibody or targeted biologic. No antigen, epitope, or species reactivity information applies.

For biochemical binding studies where Cudraxanthone D is used as a ligand or probe, any target preferences must be established experimentally and are not provided in the Product Data.